When to Wear Pinstripes

Designer Michael Kors makes the case for the executive staple and explains how to pull off Wall Street's favorite look.

Michael Kors considers pinstripes a basic. No surprise, really, from the self-made billionaire who built an empire by treating cashmere like cotton and preaching the jet-set lifestyle. The power of the pinstripe remains, as he puts it, "classic, always in style and packed with panache."

Unfortunately, Hollywood uses the pattern as a way to label bad guys. Gordon Gekko wears pinstripes. Jordan "Wolf of Wall Street" Belfort wears pinstripes. Whatever actor is playing Al Capone wears pinstripes. It's the official uniform of the avaricious.

But all those villains are stuck in period pieces. Today's pinstripe suit is much more approachable thanks to the slimmer modern cut. Nipped at the waist, with slim lapels and a snug fit through the body, pinstripes have a very different appeal.

"It's a classic pattern that can at times be a little sporty, but still feels classic," says Kors. "I think more men should play with patterns, and pinstripes are an easy one."

A classic black suit looks best with a white shirt and a dark tie, but if you add pinstripes you can start experimenting with color (and pocket squares). If you want to make it even easier on yourself, find a suit with narrower stripes. “Thin is always in," he advocates. Kors also is a fan of colored pinstripes so long as they are "solid neutral, like khaki or navy," but is quick to point out that "optic white will alway make it pop." That is, after all, the point.

In terms of accessories: simple is better. A watch in stainless steel (white gold or platinum if you're in the corner office) will help bring out pinstripes, while a pair of driving loafers and aviators diminish the intimidation factor. And don't even think about wearing them on a Saturday.

"Professionally, pinstripes are always a good idea," says Kors. "Recreationally, I'd leave it to the Yankees."